Thomas’s father William Winslow had been a member of the household of Richard II, from whom he received several annuities and offices, including that of the post of King’s pavillioner which he held from 1395 until his master lost the throne. Following the accession of Henry of Bolingbroke he retired from Court, and took no part in local administration save as a tax collector in Wiltshire in 1413. He died shortly before March 1414.
First recorded at Michaelmas 1437, a few months after his stepfather’s death, Winslow was then party to the transfer to his mother of land in Wantage,
During the 1440s Winslow was frequently recorded in association with members of his wife’s family, notably his brothers-in-law Thomas Throckmorton* and John Throckmorton II*, who both represented Worcestershire in the course of the decade. He attested the electoral indenture recording Thomas’s return to the Parliament of February 1449. Some five years earlier they had been linked together in a petition sent to Chancery by the wife of Sir William Peyto‡, the Warwickshire knight then a prisoner in France, who alleged that they and several other ‘esquires’ had assembled a gang of 300 armed men to attack her tenants on the estates she held at Campden and elsewhere in Gloucestershire as dower from her previous husband, Thomas Stafford†. Katherine noted that the principal perpetrator was a ‘feed-man’ to the abbot of Pershore, and thus to ‘my lord of Warwick’ (Henry Beauchamp), and it looks as if Winslow and the rest were acting in the interest of the young earl.
Throughout the 15 years following his alleged offence, Winslow was a member of the Worcestershire bench, as one of the quorum, which strongly suggests that he had been trained in the law. Perhaps his stepfather had encouraged him to enter the profession. Winslow was elected to the second Parliament of 1449 as a knight of the shire while he was so engaged. In 1451 he and his wife brought a suit against Sir Hugh Mortimer, alleging that he had dispossessed them of the estate at Eldersfield which they held by virtue of the settlement made at the time of their marriage. Despite being awarded damages of 100 marks at an assize of novel disseisin, six years later they had still not obtained justice, and the case had been referred to the court of common pleas. Meanwhile, Winslow had taken out a pardon as ‘formerly of Eldersfield and Ramsbury, gentleman’, on 17 Nov. 1452, but for what reason is unknown.
Before that second election, in November 1454 Winslow had appeared in the King’s bench to stand bail for John Borne, the nephew of his late stepfather, who, a prisoner in the Marshalsea, had to find four bailsmen, each prepared to put up the sum of £20 to guarantee his good behaviour.
In the second half of the 1450s Winslow fell out with Richard Beauchamp, bishop of Salisbury, who challenged his title to the estate at Ramsbury in a plea in King’s bench, which also involved Winslow’s daughter Joan Hale and her husband and father-in-law, on whom he had settled the property. The bishop obtained judgement and damages against them in Hilary term 1458.
Winslow’s estates were divided between his daughters. Elizabeth’s husband John Terumber must have died without issue for it was her children by her second husband, Humphrey, a younger son of (Sir) John Seymour I* of Wolf Hall in Great Bedwyn, to whom Even Swindon and Wendlebury descended. Her sister Isabel, who married Humphrey’s brother Ralph Seymour, sold her inheritance (the manors of Marsh Court in Eldersfield and Hill Court in Longdon) to Sir Richard Croft† in 1476. A third daughter, Agnes, married John Giffard of Twyford; and the fourth, Joan Hale, produced two daughters who married two of the sons of John Filoll* of Dorset. The division of Thomas Winslow’s estates between his various coheirs almost inevitably led to suits in Chancery between his descendants in the early sixteenth century.
